Answer to Question #236170 in Organic Chemistry for merewalesi

Question

Two stereoisomers of 1-tert-butyl-2-bromo-3-methylcyclohexane are shown below. These are referred to in the questions that follow.

(a) Draw the possible chair conformers for each of the above stereoisomers and indicate the more stable conformer in each pair by calculating total strain energy. [4 marks]

(b) Perform the ring flip for the most stable conformer for each structure and comment using relative energies of the chair conformations suggesting which form is more stable. [4 marks]

(c) If each stereoisomer is exposed to E2 elimination conditions, draw the structure(s) of the E2 elimination product(s) that may be obtained for each of them. Show clearly how you arrive at the answers (use mechanisms). [4 marks]

Answer 1

The answer is provided in the image below